Studies towards the construction of alkylidene quinolizidines: the total synthesis of homopumiliotoxin 223G
The addition of 5-methyl-2-triisopropylsilyloxyfuran (5) to N-carbobenzyloxy-2-methoxypiperidine (6a) afforded a mixture of the corresponding erythro and threo isomers 7a and 8a, respectively, in moderate to good yields (42-85%) and diastereoisomeric ratio (7a : 8a) ranging from 1.1:1 _ 6:1 dependin...
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| Format: | Article |
| Language: | English |
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Sociedade Brasileira de Química
2003-01-01
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| Series: | Journal of the Brazilian Chemical Society |
| Subjects: | |
| Online Access: | http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532003000600015 |
| _version_ | 1811302691324821504 |
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| author | Santos Leonardo S. Pilli Ronaldo A. |
| author_facet | Santos Leonardo S. Pilli Ronaldo A. |
| author_sort | Santos Leonardo S. |
| collection | DOAJ |
| description | The addition of 5-methyl-2-triisopropylsilyloxyfuran (5) to N-carbobenzyloxy-2-methoxypiperidine (6a) afforded a mixture of the corresponding erythro and threo isomers 7a and 8a, respectively, in moderate to good yields (42-85%) and diastereoisomeric ratio (7a : 8a) ranging from 1.1:1 _ 6:1 depending on the solvent system and the Lewis acid employed. The threo isomer 8a was eventually converted to (+/-)-homopumiliotoxin 223G (1) which was prepared in 5 steps and 13% overall yield from 6a. |
| first_indexed | 2024-04-13T07:33:42Z |
| format | Article |
| id | doaj.art-880706bb3d634f70843360e8f8afe271 |
| institution | Directory Open Access Journal |
| issn | 0103-5053 |
| language | English |
| last_indexed | 2024-04-13T07:33:42Z |
| publishDate | 2003-01-01 |
| publisher | Sociedade Brasileira de Química |
| record_format | Article |
| series | Journal of the Brazilian Chemical Society |
| spelling | doaj.art-880706bb3d634f70843360e8f8afe2712022-12-22T02:56:16ZengSociedade Brasileira de QuímicaJournal of the Brazilian Chemical Society0103-50532003-01-01146982993Studies towards the construction of alkylidene quinolizidines: the total synthesis of homopumiliotoxin 223GSantos Leonardo S.Pilli Ronaldo A.The addition of 5-methyl-2-triisopropylsilyloxyfuran (5) to N-carbobenzyloxy-2-methoxypiperidine (6a) afforded a mixture of the corresponding erythro and threo isomers 7a and 8a, respectively, in moderate to good yields (42-85%) and diastereoisomeric ratio (7a : 8a) ranging from 1.1:1 _ 6:1 depending on the solvent system and the Lewis acid employed. The threo isomer 8a was eventually converted to (+/-)-homopumiliotoxin 223G (1) which was prepared in 5 steps and 13% overall yield from 6a.http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532003000600015homopumiliotoxin 223GN-acyliminium ionssilyloxyfuranvinylogous addition |
| spellingShingle | Santos Leonardo S. Pilli Ronaldo A. Studies towards the construction of alkylidene quinolizidines: the total synthesis of homopumiliotoxin 223G Journal of the Brazilian Chemical Society homopumiliotoxin 223G N-acyliminium ions silyloxyfuran vinylogous addition |
| title | Studies towards the construction of alkylidene quinolizidines: the total synthesis of homopumiliotoxin 223G |
| title_full | Studies towards the construction of alkylidene quinolizidines: the total synthesis of homopumiliotoxin 223G |
| title_fullStr | Studies towards the construction of alkylidene quinolizidines: the total synthesis of homopumiliotoxin 223G |
| title_full_unstemmed | Studies towards the construction of alkylidene quinolizidines: the total synthesis of homopumiliotoxin 223G |
| title_short | Studies towards the construction of alkylidene quinolizidines: the total synthesis of homopumiliotoxin 223G |
| title_sort | studies towards the construction of alkylidene quinolizidines the total synthesis of homopumiliotoxin 223g |
| topic | homopumiliotoxin 223G N-acyliminium ions silyloxyfuran vinylogous addition |
| url | http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532003000600015 |
| work_keys_str_mv | AT santosleonardos studiestowardstheconstructionofalkylidenequinolizidinesthetotalsynthesisofhomopumiliotoxin223g AT pillironaldoa studiestowardstheconstructionofalkylidenequinolizidinesthetotalsynthesisofhomopumiliotoxin223g |